Regio- and stereochemical aspects of bromochlorination of norbornene

Article abstract of DOI:10.1007/BF02494285

Bromochlorination of norbornene whose chemo- and regio-selectivity is determined by the type of the halogenating reagent used was studied. Three isomeric bromochloronorbornanes (2-endo-bromo-3-exo-chloro-, 2-exo-bromo-3-endo-chloro-, and 2-exo-bromo-7-syn-chlorobicyclo[2.2.1.]heptanes), 2-exo-7-syn- and 2-exo-7-anti-dibromo- and -dichloro-norbornanes, and 2-bromonortricyclane were isolated and characterized by ¹H and ¹³C NMR spectra. The spectral and structural characteristics of the resulting compounds are discussed.